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Cyclohexane dicarboxylic acid derivative with bridged ring, pharmaceutical composition comprising same, and application

A compound and cycloalkyl technology, applied in cyclohexanedicarboxylic acid derivatives and pharmaceutical compositions and application fields thereof, can solve the problems of high fat solubility, weak inhibitory effect, unfavorable oral preparations and the like

Pending Publication Date: 2021-11-09
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, perillyl alcohol has weak inhibitory effect on liver tumors, blood tumors and lung tumors, and has a pungent smell, which is not conducive to making oral preparations
[0007] Triterpenoids, such as oleanolic acid (3-hydroxy-oleanane-12-en-28-acid), have antioxidant effects, and are often used as liver-protecting preparations in clinical practice. In recent years, it has also been found to have certain anti-tumor effects. Activity, because oleanolic acid belongs to pentacyclic triterpenoids, logP is relatively large, and there is a disadvantage of high fat solubility

Method used

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  • Cyclohexane dicarboxylic acid derivative with bridged ring, pharmaceutical composition comprising same, and application
  • Cyclohexane dicarboxylic acid derivative with bridged ring, pharmaceutical composition comprising same, and application
  • Cyclohexane dicarboxylic acid derivative with bridged ring, pharmaceutical composition comprising same, and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] The cyclohexane dicarboxylic acid derivative of band bridged ring of the present invention can adopt following route preparation:

[0083]

[0084] (1) prepare nordehydrocantharidin

[0085] Weigh 20g (204mmol) of maleic anhydride, add it to a 250mL round bottom bottle, add 120mL of dry ether to dissolve, then slowly add 19g (279mmol) of furan dropwise, after the addition is complete, stir at room temperature for 24h. After suction filtration, the filter cake was evaporated to dryness to obtain 30 g (181 mmol) of white solid, with a yield of 89%. Mp:120-122℃;IR(KBr,cm -1 ):3050,1860,1795; 1 H NMR (CDCl 3 ,400MHz)δ:3.19(s,2H),5.44-5.47(m,2H),6.57-6.59(m,2H).

[0086] (2) preparation of nordehydrocantharidin dimethyl ester

[0087] Weigh 1.7g (10mmol) of nordehydrocantharidin, add it to a 25mL round-bottom bottle, then add 8mL of saturated hydrogen chloride methanol solution to reflux overnight, evaporate the solvent under normal pressure, add 10mL of distilled wa...

Embodiment 2

[0126] Antitumor Activity Test of Norcantharidin Derivatives in Vitro

[0127] The experiment used the MTT method to test the inhibitory activity of the test compound on different tumor lines (human liver cancer cell HepG2, gastric cancer cell BGC803, human lung cancer cell H460, blood cancer cell HL60, ovarian cancer cell HO8901). The test was divided into positive control group, blank control group and experimental group. . The positive group was added with corresponding concentrations of perillyl alcohol, oleanolic acid and norcantharidin as positive controls; the blank control group was added with DMSO (1%); the test group was added with corresponding concentrations of test compounds.

[0128] Take the above five tumor cells in the exponential growth phase, and adjust the concentration of the cell suspension to 1×10 with RPMI-1640 medium containing 10% calf serum. 4 cells / mL; inoculate in 96-well plate, add 100 μL cell suspension to each well, place in 5% CO 2 , Cultivat...

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Abstract

The invention discloses application of a cyclohexane dicarboxylic acid derivative with a bridged ring as shown in a general formula (I), a stereoisomer and a pharmaceutically acceptable salt in preparation of anti-tumor drugs. The compounds particularly have an obvious inhibition effect on leukemia, liver cancer, lung cancer, gastric cancer and ovarian cancer. The compounds provided by the invention have high anti-tumor activity, wide anti-tumor spectrum and low toxicity, and are suitable for preparing anti-cancer drugs.

Description

technical field [0001] The invention belongs to the field of antitumor drugs, and in particular relates to a class of cyclohexanedicarboxylic acid derivatives with bridging rings, pharmaceutical compositions and applications thereof. Background technique [0002] As a complex disease with multiple etiological networks, cancer has the second highest mortality rate in the world. At present, antineoplastic drugs mainly target a single target or pathway, although such drugs have achieved good therapeutic effects (Nat. Rev. Drug Discv. 2006, 5, 993-996). However, most drugs have damage to the hematopoietic system, so that they show severe side effects clinically. In addition, most tumor drugs used clinically are immunosuppressants, which suppress the body’s immune response while controlling the proliferation of cancer cells, thereby reducing the body’s defense against tumors, and may also increase the risk of other diseases, such as infectious diseases. Morbidity risk (Bioorg. ...

Claims

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Application Information

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IPC IPC(8): C07D493/18C07D493/08C07J63/00C07D307/00C07D491/18C07C27/02C07C62/24C07C62/06C07C67/31C07C69/757A61P35/00A61P35/02A61K31/365A61K31/343A61K31/58A61K31/194A61K31/215A61K31/407
CPCC07D493/18C07D493/08C07J63/008C07D307/00C07D491/18C07C62/24C07C62/06C07C69/757A61P35/00A61P35/02C07C2602/42
Inventor 汤磊陈文章彭严彭金刚崔杏
Owner GUIZHOU MEDICAL UNIV
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